Hardcore, who had debuted in the World Wrestling Federation in 1994, introduced his on-screen "cousin" Crash Holly on August 16, 1999.[6] After arguing over who was the toughest Holly cousin,[2] the pair brawled all over the arena for the rest of the show.[6] They teamed up for the first time at SummerSlam,[7] and spent the next few weeks alternating between being rivals and partners.[8][9][10] From September on, the cousins started teaming together full-time,[11][12][13][14] during which time they took to the gimmick of claiming themselves to be well over 400 lb (180 kg), so they could be considered "superheavyweights".[2]

In early 2000, the Holly cousins began feuding over the Hardcore title. Hardcore had first won the title in early 1999, before Crash's debut;[19] however, Crash won it on February 22, 2000, defeating Test.[19] The pair soon started fighting each other for the title including in the "hardcore" Battle royal at WrestleMania 2000, where Crash started off as the champion, but Hardcore left as champion.[19] Crash regained the title the day after WrestleMania,[19] and soon after this, the Holly cousins had their last match as a team for over six months.[1]

During these months Crash concentrated on the hardcore division winning the title 22 times (after introducing the infamous "24/7 rule"), and earning the nickname "the Houdini of Hardcore".[19] Hardcore suffered a legitimate broken arm in a match against Kurt Angle and was sidelined for most of this time.[3]

In early 2001, the Hollys began feuding with the Dudley Boyz.[34] In May 2001, Crash and Hardcore, along with Bubba and D-Von Dudley became concerned about Molly's burgeoning relationship with Spike Dudley.[35] This led to the Hollys-Dudleys feud intensifying, with both Spike and Molly caught in the middle.[36][37][38] On May 28, 2001, the Dudley Boys famously put Molly through a table, with Spike lying on the table to try and protect her.[38] As Molly and Spike's relationship progressed, the feud between the Hollys and the Dudleys worsened.[39][40][41][42]

The led to the final break-up of the Holly cousins, as Molly started accompanying Spike for his matches,[5] Crash joined the Rawbrand until 2003,[2] and Hardcore was re-injured in September 2002.[3]

Crash competed on Raw and later traded to SmackDown! until his release from WWE on June 30, 2003.[2] He later died on November 6, 2003.[2] Molly eventually dumped Spike,[5] and went on to become a two-time Women's champion.[43][44] On April 12, 2005, Molly left the company and retired from full-time wrestling.[5][45] Hardcore was the final Holly to be released from the company, on January 16, 2009.[3]